The Time I Was An Online Dating Coach … For My Mom

“Nat, it’s an emergency,” my 66-year-old mother’s voice said as I listened to her phone message outside of my office.

After she called five times in a row, I figured it was important and snuck out of work to hear it. I feared her next sentence. She lived with her mother, my 92-year-old grandmother, who was more like my mom than my mom, and she’d been falling down multiple times a week. “A Match-dot-com guy wrote to me!” my mom’s message continued. “Call me! I don’t know what to write back!”

I had a freelance job writing people’s online dating profiles for e-Cyrano.com, and several clients were in my mom’s age bracket, Baby Boomers. I thought if they could Internet date, so could she. What I didn’t expect were the emergency phone calls 24/7. “He wrote, ‘I find you beautiful and charming,'” my mom said when I called her back. “Then he put a picture of a rose. It’s cute. It looks like a cartoon. He called me ‘beautiful,’ Nat! Do you know how long it’s been since a man said that?”

Though she was beautiful, I wanted to tell her that he probably messaged several women that same, one-line sentence, which took minimal effort. (Yes, the rose was a nice touch, but still.) Regardless, I was happy for my mom for getting out of her comfort zone. She was barely Internet-savvy, let alone Internet-dating-savvy. She had no idea what she was doing, from choosing a username (a combination of her first and last name, “delusins,” which made one guy ask if she was delusional!) to almost wiring an online match $1,000 when he was clearly trying to scam her. Then there was the time my grandmother’s nurse was over at the house and suggested my mom post some pictures of herself in a bathing suit (and my mom is not that kind of girl). I had to intervene and began coaching her on how to online date: how to identify the cut-and-paste email guys, avoid falling into the online dating pen pal trap, and post a few, modest pictures (a close-up, a medium shot, and a faraway one—and certainly no swimsuit shots).

One day, a 65-year-old client of mine said, “If you think dating’s tough at your age, imagine what it’s like at your mom’s age. I know.” I thought about how, ever since my mom’s second divorce when I was 9, she’d lived with her mother. Sometimes she’d have boyfriends who she’d meet through work or friends. But she had recently retired, and her friends were coupled up. Her mother was the one constant in her life, for better or worse, in sickness and in health. Most of the phone calls my mom received were from my grandma’s Medicare reps or doctors, not eligible bachelors.

My mom didn’t need to online date, but I was glad she did, as I think we both realized her current live-in companion of the last 30 years, my grandma, would soon be going to an assisted living facility. My mother would be all alone. Though she knew how to be single, I thought dating would be a nice distraction from the heaviness around her (my grandma’s falls, the paramedics’ weekly visits, my grandma’s doctors suggesting alternate living options). It would be nice for my mom to have someone to do things with—movies, dinners, concerts—and to get phone calls from people not wanting to discuss her mother’s health care options.

“Nat, what do I write back?” my mom said during another phone call.

“He told you he plays golf,” I said. “Ask him about his handicap.”

She then emailed him, “My daughter said to ask you about your handicap.”

Mother! I reminded her to rewrite what I said in her own words, so the guy didn’t think I was the one who liked him. I thought back to grade school, how my mom would double-check my English homework, making sure every sentence was correct. “Every word counts,” she’d say. I told her the same thing now as we composed a thoughtful response to the man in question, being as specific as possible to show that we not only read his email, but also his profile.

Another night, my mom said, like a squealing teenager, “Nat, he wants to meet … in person!” I was so elated, as though I was the one getting the date. Yet I felt like an overprotective parent, seeing my mom off into the unknown, choppy dating waters. I would advise her on what to wear (something feminine but modest) and remind her to meet in a public place, tell a friend where she was going, have a time limit and an out if it wasn’t going well, and to “just say no,” something she’d told me 20 years prior when I went on dates back in high school.

Afterward, she’d call me to recap and would usually say, “Nat, it was awful!” (offset by an occasional “Nat, I’m in love!”). No, I didn’t ask her for all the details from her dates, but it was intriguing to hear some of them—like where they went, if he was a gentleman, if he paid or insisted they split it, and what they had in common. I realized that some guys in their 60s were just as romantic as ones in my age bracket, in their 30s and 40s (showing up with a rose, not just a cartoon one, or standing up when she got up to use the restroom). However, at the same time, some were just as slimy—too touchy and ungentlemanlike. As I found myself saying, “Don’t feel obligated to kiss him,” “Nope, not the one for you,” and “Don’t settle,” I realized I needed to be listening to the same advice.

A few months into my mother’s online dating, my grandma did go into an assisted living center. And now, my mom brings her boyfriend with her to visit.